Classifications

• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
  • C08F222/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
  • C08F222/04—Anhydrides, e.g. cyclic anhydrides
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
  • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
  • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
  • C08F220/10—Esters
  • C08F220/12—Esters of monohydric alcohols or phenols
  • C08F220/14—Methyl esters, e.g. methyl (meth)acrylate
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
  • C08F2/00—Processes of polymerisation
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
  • C08F210/00—Copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
  • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
  • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
  • C08F220/04—Acids; Metal salts or ammonium salts thereof
  • C08F220/06—Acrylic acid; Methacrylic acid; Metal salts or ammonium salts thereof
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
  • C08F222/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
  • C08F222/04—Anhydrides, e.g. cyclic anhydrides
  • C08F222/06—Maleic anhydride
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
  • C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
  • C08J5/18—Manufacture of films or sheets

Definitions

• the present invention relates to a novel copolymer and a method of manufacturing the same. More particularly, the present invention relates to a novel copolymer that has the excellent transparency, mechanical property, adhesion property and heat resistance and can be applied to various types of optical materials, and a method of manufacturing the same.
• This application claims priority from Korea Patent Application No. 10-2007-0047525 filed on May 16, 2007 in the KIPO, the disclosure of which is incorporated herein by reference in its entirety. Background Art
• the copolymer of ethylene and alkyl acrylate or ethylene and alkyl methacrylate is obtained by using the high temperature and high pressure reaction.
• the reaction by simultaneously adding ethylene and an acryl monomer by using a tube type of reactor or an autoclave reactor under the severe condition of 1000 atm or more and 100 0 C or more is disclosed.
• the polymer that is obtained under this condition is a copolymer polymerized by using the acryl monomer that is the polar monomer in an amount of 3 to 35% based on ethylene.
• the ethylene copolymer that is manufactured by using a known method includes few polar groups. That is, since the content of polar monomer is not high, the crystallinity of polyethylene remains in the copolymer. Thus, there is a limit in use of the copolymer in an optical material such as a transparent film. Accordingly, in respects to the polymer that is obtained according to the known high temperature and high pressure method by using tube type of reactor or autoclave, products that do not affect the transparency have been mainly developed.
• the present invention provides a copolymer that includes 0.1 to 30 mole% of at least one alkene monomer, 30 to 95 mole% of at least one acrylate monomer, and 0.1 to 40 mole% of at least one unsaturated acid anhydride monomer.
• the present invention provides a method of manufacturing a copolymer, which includes polymerizing at least one alkene monomer 0.1 to 30 mole%, at least one acrylate monomer 30 to 95 mole% and at least one the unsaturated acid anhydride monomer 0.1 to 40 mole% in the presence of a Lewis acid or a metal oxide by using a radical polymerization initiator.
• a copolymer according to the present invention is an amorphous polymer that has the high content of polar group, and has the excellent transparency and the improved adhesion property and heat resistance. Therefore, the copolymer can be applied as various types of optical materials.
• the conventional alkene- acrylate polymer has a disadvantage in that the glass transition temperature decreases as the content of ethylene increases, titwever, the copolymer according to the present invention has high glass transition temperature of 100 or more degree by comprising the unsaturated acid anhydride so as to be applied to optical materials.
• the polymerization can be performed by using an appropriate amount of alkene monomers used to ensure the physical properties required under the mild reaction condition, in the case of when the metal oxide, the metal oxide can be recovered and reused to ensure economic efficiency, and a problem regarding the impurity in the polymer can be solved. Accordingly, it is possible to manufacture the polymer having the high purity.
• FIG. 1 illustrates a hydrogen nudear magnetic resonance spectrum ( H-NMR spectrum) of an ethylene-methyl methacrylate random copolymer that is obtained in
• FIG. 2 illustrates the differential scanning calorimetry (DSQ analysis results of an ethylene-methyl methacrylate-maleic acid anhydride random copolymer that is obtained in Examples 1 and 6;
• FIG. 3 illustrates the gel permeation chromatography (GPQ analysis results of an ethylene-methyl methacrylate-maleic acid anhydride random copolymer that is obtained in Example 2;
• FIG. 4 illustrates the UV- Visible spectrum analysis results of the film that is produced by using an ethylene-methyl methacrylate-maleic acid anhydride random copolymer that is obtained in Example 5; [18] FIG.
• FIG. 5 illustrates the gel permeation chromatography (GPQ analysis results of an ethylene-methyl methacrylate-maleic acid anhydride random copolymer that is obtained in Example 6; [19] FIG. 6 illustrates the IR spectrum analysis results of an ethylene-methyl methacrylate-maleic acid anhydride random copolymer that is obtained in Example 7; and [20] FIG. 7 illustrates the differential scanning calorimetry (DSQ analysis results of an ethylene-methyl methacrylate-maleic acid anhydride-glyddyl methacrylate random copolymer that is obtained in Example 8.
• a copolymer according to the present invention includes an alkene monomer, an acrylate monomer, and an unsaturated acid anhydride monomer.
• the contents of the alkene monomer, the acrylate monomer and the unsaturated acid anhydride monomer be 0.1 to 30 mole%, 30 to 95 mole%, and 0.1 to 40 mole% respectively.
• the inclusion of the alkene monomer, acrylate monomer and the unsaturated acid anhydride monomer in the copolymer according to the present invention means that the copolymer according to the present invention is formed by polymerizing the monomers. Ibr convenience of the understanding, the terms of the monomers are used to express the structures thereof.
• the glass transition temperature (Tg) of the copolymer according to the present invention is in the range of 80 to 22O 0 C, preferably 100 to 18O 0 C and more preferably 120 to 18O 0 C. In order to effectively use the copolymer as an optical material, it is preferable that the glass transition temperature be 100 0 C or more. In addition, it is preferable that the copolymer according to the present invention have a number average molecular weight in the range of 5,000 to 400,000 and a weight average molecular weight in the range of 10,000 to 800,000. In addition, it is preferable that the copolymer according to the present invention have a temperature at which an initial weight is reduced by half (Td ) in the range of 300 to 55O 0 C.
• examples of the alkene monomer include, but are not limited to alkenes sirh as 1 -alkene that has a double bond at an end of a carbon chain thereof, 2-alkene and 3-alkene that has a double bond at a middle part of a carbon chain thereof, and the like.
• Examples of 1 -alkene may include ethylene, propylene, 1-butene, 1-pentene,
• alkene that has the double bond at the middle part of the carbon chain thereof may include 2-butene, 2-pentene, 2-hexene, 3-hexene, 2-hepthene, 2-octene, 2-nonen and the like.
• the content of the alkene monomer is in the range of 0.1 to 30 mole% and preferably 10 to 30 mole%.
• the polymer includes only the monomers having the polar group without the alkene monomer, there is a problem in that the formed film is easily broken.
• the content of the alkene monomer in the copolymer is 10 mole% or more, the polymer is not easily broken when the monomer is applied to the layered film of the optical material. IHbwever, the alkene monomer may be included in an amount of less than 10 mole% in respects to products that do not require the nonbreaking.
• the acrylate monomer may be a compound having a double bond between conjugated carbons and carbonyl group of an ester group, and a substituent group thereof is not limited.
• acrylate monomer means acrylate and an acrylate derivative, and includes alkyl acrylate, alkyl methacrylate, alkyl butacrylate and the like.
• examples of the acrylate monomer include a compound that is represented by the following Ibrmula 1. [30] [Ibrmula 1]
• R , R and R are the same or different from each other, and are each independently a
• R , R and R may be an
• R is a hydrogen atom or an alkyl group having 1 to 6 carbon atoms.
• R is an epoxy group include glyddyl methacrylate and glyddyl acrylate.
• examples of the acrylate monomer include alkyl acrylate including a straight- or branched-chained alkyl group having 1 to 12 carbon atoms, alkyl methacrylate including a straight- or branched-chained alkyl group having 1 to 12 carbon atoms, or alkyl butacrylate including a straight- or branched-chained alkyl group having 1 to 12 carbon atoms.
• the content of the acrylate monomer in the copolymer be in the range of 30 to 95 mole%, preferably 40 to 95 mole%, more preferably 50 to 90 mole% , and most preferably 50 to 80 mole%.
• the copolymer is useful to apply electric devices.
• the amount of the acrylate comonomer is less than 30 mole% based on the total amount of the monomers, the adhesion property and the transparency are poor.
• the amount of the acrylate comonomer is more than 95 mole%, there is a problem in that the mechanical property of the polymer decreases and the polymer is easily broken.
• the amount of the acrylate monomer is preferably 95 mole% or less and more preferably 90 mole% or less so as to redire the breaking property during the formation of the film.
• the unsaturated add anhydride has one or more double bonds and can be used to perform radical polymerization by using the double bond. It is to be understood that even though there is no mention regarding the unsaturated add anhydride in the spedfication, the unsaturated add anhydride has one or more double bonds unless otherwise spedfied.
• carboxylic add anhydride may be used as the unsaturated add anhydride, and monovalent or polyvalent carboxylic add anhydride may be used.
• maleic anhydride or a derivative thereof may be used, for example, the compound that is represented by the following Ibrmula 2 may be used.
• R and R are each independently a hydrogen atom or an alkyl
• the content of the unsaturated add anhydride monomer is in the range of 0.1 to 40 mole%, and preferably 10 to 30 mole%.
• the copolymer has a high glass transition temperature.
• the copolymer may be used as the optical material.
• the copolymer since the copolymer has many polar functional groups, the copolymer has the excellent adhesion strength in respects to metal or the like. Thus, the copolymer is useful to be applied to electric devices.
• the copolymer that consists of the repeating units of the above-mentioned monomers may include a repeating unit that is represented by the following Ibrmula 3.
• the copolymer may be a random copolymer.
• the copolymer according to the present invention may include various types of repeating units that are represented by Ibrmula 3.
• the copolymer may include a block or blocks as long as the transparency is maintained. It is preferable that the copolymer according to the present invention have the transparency of 80% or more during the formation of the film.
• the copolymer according to the present invention has the high content of polar group, there is no crystallinity in alkene such as ethylene. Thus, a polymer film is formed by using the copolymer according to the present invention is transparent. Additionally, since the copolymer includes the unsaturated add anhydride, the copolymer has the high glass transition temperature and the improved adhesion property and preferably used for a polarizing plate and an optical film having a multilayered structure.
• the alkene-acrylate-unsaturated add anhydride copolymer according to the present invention may include one type of alkene, one type of acrylate, and one type of unsaturated add anhydride as the monomer component, and the copolymer may include two or more type of at least one of alkene, acrylate and unsaturated acid anhydride. Particularly, it is preferable that two or more type of acrylate monomers are used and at least one acrylate monomer is alkyl acrylate monomer. Additionally, within the range of the physical properties of the polymer and the object of the present invention, the copolymer may further include a comonomer.
• Examples of the comonomer may include unsaturated organic acid, maleimides, methyl maleimides, ethyl maleimides, butadiene, styrene and the like.
• Monovalent or polyvalent carboxylic acid may be used as the unsaturated organic acid.
• the copolymer may be manufactured by polymerizing the alkene monomer, the acrylate monomer, and the unsaturated acid anhydride monomer in the presence of the Lewis acid or the metal oxides by using a radical polymerization initiator.
• the Lewis add or the metal oxides are used to avoid a high temperature and high pressure severe condition of a known technology.
• the process is simple in the manufacturing method.
• all of the used metal oxides may be easily recovered by using only a filtering apparatus after the polymerization and reused, the manufacturing cost can be significantly reduced, the purification can be easily performed, and the copolymer having the high purity can be provided.
• stability in respects to water and air is excellent, the efficiency is high. Since the polymerization process may be simplified, the desirable industrial applicability is ensured.
• the metal oxide acts as the Lewis acid that provides an acid site and is included in the Lewis acid in the polymerization reaction, titwever, in comparison with the typical other Lewis acids, since there are no change in the structure and the composition even after the polymerization reaction, there are additional advantages in that the separation can be easily performed and the reuse can be performed.
• the metal oxide is called the metal oxide or the complex metal oxide so as to be discriminated from the other typical Lewis acids.
• the metal oxide be a compound represented by the following
• M is one or more selected from the group consisting of alkali earth metal, transition metal, Group 13 metal and Group 14 metal;
• N is a Group 5 or 6 atom;
• O is an oxygen atom
• x, y and z are values that are determined by an oxidation state of M and N with x > 0, y > 0, and z > 0.
• the metal oxide include one or more selected from the group consisting of metal oxides such as aluminum oxide (Al O ),
• Y O yttrium oxide
• ZrO zinc oxide
• HfO halfnium oxide
• SiO silicon oxide
• B O boron oxide
• CeO cesium oxide
• Dy O dysprosium oxide
• Er Errbium oxide
• Eu O europium oxide
• Gd O gadolinium oxide
• Ho O holmium oxide
• La O lanthanum oxide
• Lu O lutetium oxide
• Nd O neodymium oxide
• NiO manganese oxide
• TiO titanium oxide
• complex metal oxides such as dysprosium aluminate (Dy Al O ), yttrium aluminate (Y Al O ), aluminum titanate (Al O • TiO
• the metal oxide is a solid type
• the metal oxide can be completely recovered by using a physical method using only a filtering apparatus, and the recovered metal oxide can be used to perform the polymerization.
• the recovered metal oxide may be reused 20 times.
• the Lewis acid include a Lewis acid that includes one or more metal cations selected from the group consisting of scandium, titanium, vanadium, chrome, manganese, iron, cobalt, copper, zinc, boron, aluminum, yttrium, zirconium, niobium, molybdenum, cadmium, rhenium and tin, and one or more metal anions selected from the group consisting of halides, triflates, HPO 2" , H PO 2" , CF COO " , C H
• Lewis acid examples include
• the metal oxide or the Lewis acid be used in an amount of 0.01 to 200 mole% based on the acrylate comonomer.
• the content of the monomers included as the repeating unit in the manufactured copolymer can be appropriately controlled and adjusted according to the required physical properties.
• the metal oxide or the Lewis acid can control the amount of the alkene monomer required to ensure the desirable physical properties of the copolymer to be manufactured, and allow the polymerization reaction to be performed at low temperature under low pressure as compared to a known technology.
• radical polymerization initiator examples include peroxides, azo compounds and the like.
• examples of the peroxide compound may include hydrogen peroxide, decanonyl peroxide, t-butyl peroxyneodecanoate, t- butyl peroxypivalate, 3,5,5-trimethylhexanoyl peroxide, diethyl peroxide, t- butylperoxy-2-ethyl hexanoate, t-butylperoxy isobutylate, benzoyl peroxide, t-buty lperoxy acetate, t-butylperoxy benzoate, di-t-butyl peroxide, t-amylperoxy neodecanoate, t-amylperoxy pivalate, t-amylperoxy-2-ethyl hexanoate, 1,1,3,3-tetramethylbutyl hydroperoxide, al
• AIBN 2,2'-azo-bis(isobutyronitrile)
• the preferable initiator is the azo compound.
• a mixture of the initiators may be used.
• the radical polymerization initiator may be added to the reaction stream in an appropriate form, for example, in a pure form, in a form in which the initiator is dissolved in the appropriate solvent, and/or in a mixture form of the monomer or comonomer feed stream and the initiator. It is preferable that the radical polymerization initiator used to manufacture the copolymer be added in an amount of 0.01 to 10 mole% based on the acrylate monomer, titwever, the amount of the radical polymerization initiator is not limited but may vary if necessary.
• the polymerization reaction of the copolymer be performed in the presence of a solvent, in particular, an organic solvent.
• a solvent in particular, an organic solvent.
• the solvent include one or more solvents that are selected from the group consisting of toluene, chlorobenzene, n-hexane, heptane, tetrahydrofuran, ether, methanol, ethanol, chloroform, and methylene chloride, but are not limited thereto. That is, the type of solvent is not limited as long as the solvent is capable of being used in the art to which the present invention belongs.
• the reaction pressure is not limited.
• the high pressure reaction condition is required. IHbwever, in the case of when the alkene monomer is present in a liquid phase under the reaction condition, the reaction pressure is not limited.
• the polymerization reaction may be performed under the mild condition of 200 atm or less and 15O 0 C or less, and preferably 50 atm or less and 100 0 C or less.
• the polymerization reaction is a simple process and it is easy to control the physical properties of the manufactured copolymer.
• the metal oxide since the metal oxide has excellent stability against moisture, the metal oxide is effective and can be reused.
• the polymerization reaction in the case of when the alkene monomer is present in a gas phase under the reaction condition, it is preferable that the polymerization reaction be performed under pressure in the range of 5 to 200 atm and the temperature condition in the range of 30 to 15O 0 C. In particular, the reaction is performed under pressure in the range of 20 to 50 atm and the temperature condition in the range of 50 to 8O 0 C.
• the polymerization pressure is less than 5 atm, the content of the alkene monomer decreases.
• the polymerization pressure is more than 200 atm, additional instruments are required.
• the polymerization temperature is less than 3O 0 C, initiators may not be activated.
• the polymerization temperature is more than 15O 0 C, it may be difficult to control the polymerization process.
• ethylene or propylene is used as the alkene monomer
• methyl methacrylate or methyl acrylate is used as the acrylate monomer
• the maleic anhydride is used as the unsaturated acid anhydride monomer
• aluminum oxide is used as the metal oxide
• the polymerization is performed by using AIBN as the polymerization initiator under pressure in the range of 5 to 50 atm and the temperature in the range of 50 to 8O 0 C.
• the copolymer according to the present invention has high glass transition temperature and toughness and excellent light transmissivity and adhesion property. Therefore, the copolymer according to the present invention may be used to manufacture an optical film. Since the optical film that includes the copolymer according to the present invention is manufactured by using the copolymer resin that has the high light transmissivity, glass transition temperature, and toughness, the optical film has the high light transmissivity, and the excellent adhesion property due to the high content of the monomer having the polar functional group. Thus, the copolymer is suitable to be used for a layered film sirh as a polarizing plate. Accordingly, the copolymer may be used to manufacture a retardation compensation film having the birefringence by using the stretching, a polarizing film by the post- treatment using an iodine solution, and various types of optical films. Mode for the Invention
• the molecular weight and the molecular weight distribution were obtained by using the analysis of the GPC (gel permeation chromatography) manufactured by Waters, Go., Ltd.
• the analysis temperature was 25 0 C
• tetrahydrofuran (THF) was used as the solvent
• the standardization was performed by using polystyrene to obtain the number average molecular weight (Mn) and the weight average molecular weight (Mw).
• COMPARATIVE EXAMPLE 3 [88] The polymerization was performed by using the same method as Comparative Example 2, except that the addition amount of alumina was reduced.
• Comparative Example 1 relates to the production of a random copolymer of maleic acid anhydride (MAH) and methyl methacrylate (MMA), and since the copolymer has the high glass transition temperature, the copolymer has high heat resistance. However, since the copolymer is brittle, it is difficult to form a film by using the copolymer.
• MAH maleic acid anhydride
• MMA methyl methacrylate
• Comparative Examples 2 and 3 relate to an ethylene-methyl methacrylate random copolymer.
• the ethylene-methyl methacrylate random copolymer having the ethylene content of 20mole% was polymerized.
• Comparative Example 3 relates to the result regarding the free radical polymerization while the addition amount of alumina was reduced as compared to the polymerization condition of Comparative Example 2, and the ethylene-methyl methacrylate random copolymer having the ethylene content of 9.7 mole% which was lower as compared to Comparative Example 2 was polymerized.
• Comparative Example 3 since the content of ethylene was reduced, the glass transition temperature was increased as compared to that of Comparative Example 2.
• THF Tetrahydrofurane
• FIG. 2 illustrates the differential scanning calorimetry (DSQ graph of an ethylene-methyl methacrylate-maleic acid anhydride random copolymer that is obtained in Examples 1 and 6
• FIG. 3 illustrates the gel permeation chromatography (GPQ analysis results of an ethylene-methyl methacrylate-maleic acid anhydride random copolymer that is obtained in Example 2
• FIG. 4 illustrates the UV- Visible spectrum analysis results of an ethylene-methyl methacrylate-maleic acid anhydride random copolymer that is obtained in Example 5
• FIG. 2 illustrates the differential scanning calorimetry (DSQ graph of an ethylene-methyl methacrylate-maleic acid anhydride random copolymer that is obtained in Examples 1 and 6
• FIG. 3 illustrates the gel permeation chromatography (GPQ analysis results of an ethylene-methyl methacrylate-maleic acid anhydride random copolymer that is obtained in Example 2
• FIG. 4 illustrates the UV- Visible spectrum analysis results of an ethylene-methyl
• FIG. 5 illustrates the gel permeation chromatography (GPQ analysis results of an ethylene-methyl methacr ylate-maleic acid anhydride random copolymer that is obtained in Example 6
• FIG. 6 illustrates the IR spectrum analysis results of an ethylene-methyl methacrylate-maleic add anhydride random copolymer that is obtained in Example 7.
• the ethylene-methyl methacrylate-maleic add anhydride copolymer having the glass transition temperature of about 12O 0 C or more was synthesized.
• the low glass transition temperature problem that was the dis- advantage of the high transparent film synthesized in Comparative Example was solved, and the 50% thermal decomposition temperature that was measured by the TGA was 400 0 C or more which was high.
• the content of the ethylene was increased, the glass transition temperature was reduced, and as the content of maleic add anhydride and acrylate was increased, the glass transition temperature was in creased.
• the polymer having the desired heat resistance and physical properties can be synthesized according to the change in polymerization condition.

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